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After dinner we went to watch a porn movie. In the movie, Jen wore no panties and a short mini skirt. Needless to say my hands were in her wetness most of the time. I sat on one side, and Theo on the other. I kept whispering to her to rub his cock but she was afraid. He did not try to touch her. After the movie we went back to our room and invited Theo. He seemed a bit afraid but I coaxed him in. We sat down on the bed and before Jen sat down I pulled her towards me and started caressing the back of her legs. I moved my hands higher to her taut petite ass. She tried to pull away and push my hands away but I held on and continued. I knew that Theo who was sitting on the other bed could see her ass, which I continued caressing in front of him. I could see that he was getting hard. I stood up and started to kiss Jen and then gently laid her on the bed. I lifted her skirt and told Theo to look at her gorgeous pussy. I opened her legs and started to lick her. She started cumming. I took. At this point, I was open to anything, and again without hesitation, I said yes. He put the condom on, but neither one of us knew how to proceed. I bent over the bed and he tried to push it in, but the pain was too much. So I sat him down on the bed and sat on his cock, facing away from him. I tried to just sit on it, but that hurt too much, so I just kinda rubbed the head against my asshole for a while. As the lube from the condom lubed up my ass, it opened up a little, and I was able to slide down a little more. I started to bounce up and down on him and it felt so good! I finally just let all my weight come down on his cock, and I felt it pop in and slide all the way up my ass! OUCH! It hurt so bad, I made him stop. He calmed me down and convinced me that the condom was the problem. So he took it off, spit on it a lot and slowly started working his way in and out of me again. The pain subsided and was gradually replaced by a pleasant feeling. I relaxed and he was able to establish.
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